


The One Where Dean Bottoms

by HolyFuckingHell



Series: Dean and Cas’s Time [12]
Category: Supernatural
Genre: Anal Sex, Awkwardness, Bottom Dean Winchester, First Time Bottoming, Fluff, Fluff and Smut, Funny, M/M, Nervous Dean Winchester, Oral Sex, Sex, Smut, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2021-02-23
Updated: 2021-02-23
Packaged: 2021-03-13 23:01:48
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 10,156
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29658651
Author URL: https://archiveofourown.org/users/HolyFuckingHell/pseuds/HolyFuckingHell
Summary: Beginning of the relationship stuff!! Dean bottoms for the first time. He’s nervous about it, it’s great!
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Series: Dean and Cas’s Time [12]
Series URL: https://archiveofourown.org/series/2069001
Comments: 11
Kudos: 120





	1. Chapter 1

**Notes for the Chapter:**

> Thank y’all for clicking on this fic, I hope it doesn’t disappoint ;)

The only thing Dean likes better than sleeping with Cas is  _ sleeping with Cas. _

He  _ loves _ that Cas spends the night in bed with him every night.  _ Every night. _ Even if they don’t have sex. And even if they aren’t in the bunker, Dean was  _ not _ expecting that but he was delighted. They were at some motel in some random city, Dean went to bed for the night, then Cas crawled right under the blanket with him. Like it was normal. Dean didn’t say anything more than a dorky “Hey,” to Cas when he unexpectedly laid down and snuggled up to him. Dean didn’t want to make a big deal about it. He tried to stay cool because on the inside it felt like the best thing ever. Pure, unadulterated bliss. 

But what’s even better than that is the  _ sex. _ Dean, not shockingly,  _ loves _ having sex with Cas. It’s so fun. It’s the  _ real  _ best thing ever. Every time he so much as looks in Cas’s direction he wants to jump his bones. And they have sex  _ a lot. _ Dean didn’t actually register how much sex they were having until he had to buy more lube and condoms. One time, Cas randomly shoved Dean into a bookshelf in the library and started kissing him like he  _ meant it.  _ Meaning he wanted to have sex. In the end, Dean wound up just giving Cas a blowjob. And  _ now, _ Dean carries around a small thing of lube  _ just in case _ because he doesn’t want to make that mistake again. 

“Dean,” Cas straddles Dean’s lap when he sits down on the bed. “I have a question for you.”

“Okay…” Dean says nervously. Cas asks  _ a lot _ of questions when they have their sexy times. And every single one of them makes Dean  _ wildly _ uncomfortable to answer. But, he usually only asks Dean questions  _ after _ they have sex, not before. So Dean has no idea what’s coming. 

“Why do you wear those?” Cas points to Dean’s hands. He just got a condom and lube from his drawer and that's what he’s holding. 

“Uhm, condoms?” Dean asks, already feeling squirmy. 

“Yes, what are they for?”

“Well,” Dean adverts his eyes nervously. “They’re… Birth control… So no one gets pregnant,” Dean chuckles. 

“Dean,” Cas rolls his eyes. “It is impossible for either of us to get pregnant.”

“I know,” Dean chuckles and sits back against the headboard. “I was just kidding.”

“So what else are these for?” Cas takes the condom from Dean’s hand and holds it up likes he’s inspecting it. 

“Protection…”

“From what?”

“Uh, STDs.”

Cas tilts his head, “I don’t have any sexual diseases, and if I did they wouldn’t be able to transmit to  _ you.” _

“Why?” Dean asks, confused. 

“I’m an angel of the lord.”

“Oh.”

“And  _ you _ also don’t have any sexual diseases.” 

“One time,” Dean chuckles, “When I was like… twenty-something, for about a week, I thought I had the clap. Turns out I was just being paranoid.” 

“Why did you think that?”

“Uh,” Dean shakes his head and laughs, “Let’s not unpack all that.”

“Alright,” Cas chuckles. “Well, did you think  _ I _ had an STD?”

“No,” Dean says quickly. “I didn’t.”

“Why do you wear these then?” Cas raises an eyebrow. He just wants Dean to give him a straight answer and he doesn’t know why he’s avoiding it. 

“Well,” Dean rolls his eyes with a sigh, “Cas… You don’t  _ really _ want me to come  _ inside of you, _ do you?”

“What do you mean?”

“Well… The condom…  _ Stops  _ all that,” Dean shrugs, “So, I don’t know, you don’t have to deal with it.”

“Why does it sound like you think this is a bad thing that I do not wish to ‘deal with?’”

“Because it’s come! In your ass! I doubt you want that.”

“I want that,” Cas says plainly. 

Dean swallows and shakes his head. Surely he heard Cas wrong. “What?”

“I. Want. That.”

No way. He’s just misunderstanding him. “Want  _ what?” _ Dean asks. 

“I want you,” Cas touches his hand to Dean’s chest, “To ejaculate into  _ me.” _ Cas points to himself. 

“You- You-” Dean tilts his head. “You  _ what?” _

It’s like Dean’s brain stopped working. Cas sighs. “I would like to have sex without a condom because I see no reason why we would need that. Unless you  _ like  _ the way it feels, is that the case?”

“N-” Dean just shakes his head. 

“Then…” Cas sets the condom on the side table, “If you would like to, I think we should have sex  _ without _ it.”

“Without…” Dean bites his bottom lip, just staring at Cas. 

“Yes,” Cas nods. “Without the condom.”

“Without it,” Dean repeats. He seems dazed. 

“Yes,” Cas nods again. “I think it will be a new sensation for both of us. And also,” Cas shrugs, “Intimate.” 

“Intimate,” Dean nods, mouth hanging open, staring at Cas. 

“Right,” Cas tilts his head slightly. Dean is looking at him really funny. Just staring into his eyes in complete bewilderment. He’s frozen. “Dean?” Cas asks. 

“Mm?” Dean mumbles. 

“Would you still like… To fornicate? Right now?” Dean’s breath picks up and Cas can hear his heartbeat. Dean nods. “Without… A condom?” Cas asks. Then he can feel Dean start to get hard through his jeans.

Dean nods again. “Without-” Dean swallows and keeps nodding. 

“Are you,” Cas looks sort of worried. “Are you well, Dean?”

“Yes,” Dean answers quickly. “Are you?”

“Ye-” Cas is confused. “Yes. I’m Well… Will you kiss me so we can get started?”

“Yeah,” Dean nods but doesn’t move. 

“Dean?”

“Yeah?”

“What’s going on?”

“You-” Dean swallows. “You broke me.”

“What?” Cas chuckles.

“I- I don’t know.” Dean starts wiggling, “I wanna… I wanna fuck you without a condom. I never thought about it.” 

“But you  _ do _ want to, correct?”

“Yeah,” Dean nods. “And I wanna… I wanna come in- In-” Dean swallows. “I wanna come inside of you. You want that?”

“Yes,” Cas nods. 

Dean’s heartbeat is still really loud. “How come you never said anything about this before?”

“I did not want to make you uncomfortable as you seemed pretty attached to the condom.”

“Dude, I’d  _ so _ much rather not use a condom. I’ve just-” Dean shrugs, “I kinda always have.” 

“Okay,” Cas nods, leaning into Dean, “If you kiss me really well, I will ride your penis again.”

“Mh,” Dean hums, “I’d like that…” Dean chuckles. “But, uh, you can just say ‘I’ll ride  _ you.’ _ You don’t have to say, uh, ya know.”

“‘Your penis?’” Cas asks for clarification. 

“Yeah,” Dean nods. 

“Noted,” Cas smiles and kisses Dean. 

Dean  _ loves _ when Cas rides him. He’s only  _ just _ started doing it, but he likes it  _ so very much. _ He has less to do when Cas rides him, and if he’s being honest, that’s one of the appeals. Cas takes care of almost everything. And Cas seems to like it too. He gets to have more control which is one of his biggest turn-ons. And Dean  _ loses _ control and  _ that’s _ one of  _ his _ biggest turn-ons. But neither of them realizes that yet. 

“Holy fuck, Cas,” Dean pants. “Fuck, Cas!” Dean giggles. “Holy fucking hell, dude!” 

“Yes?” Cas chuckles. 

“Cas,” Dean bits his lip. “Cas, Cas, Cas! You don’t even know.”

“I don’t know what?” Cas asks. 

“Come ‘ere,” Dean pulls Cas by his arm until he’s laying down on him instead of his previous sitting position. “Cas, oh my gosh,” Dean pants then starts kissing him. 

“Am I to assume your orgasm was adequate?” Cas asks. 

“Shut your dumb face,” Dean rolls his eyes, “You know that it was.”

Cas smiles, “Tell me.”

“Tell you what?” Dean asks, smiling like a nerd and he knows it.

“Tell me  _ everything.” _

“Cas,” Dean chuckles. “That was  _ so fun. _ That was  _ so good!” _ Dean thinks. “I don’t know if you could feel a difference, but I came  _ so hard!” _ Dean kisses him again. “And we are so good at sex, it’s unreal.”

“We are  _ quite _ good at this, yes,” Cas agrees. 

“No!” Dean shakes his head, “I changed my mind.”

“You do  _ not _ think we are good at fornicating?”

“No,” Dean shakes his head,  _ “You _ are good at this.  _ I’m _ just lucky and along for the ride. No pun intended.”

“Intend your puns, you coward.” 

“What?”

“I know you like puns, Dean. You can’t fool me.”

“What the fuck?” Dean laughs. 

“Also, I don’t think that’s true. I think we have simply gotten into a rhythm and know each other’s bodies better.”

“No, Cas. You’re fucking good at this. I’m average. Or at least I like to  _ think _ I’m average.  _ Fuck. _ Don’t say anything.  _ Fuck, _ forget I said that. If you say I’m below average I’m gonna be upset. If you agree with me, I’m gonna be upset. If you say I’m above average, I’m not gonna believe you.” 

“Why did you say that then?” Cas asks, giggling. 

“I don’t know. I’m excited and stupid! Damn monkey brain!” Dean shrugs and hugs around Cas a little tighter. “Wait, but now I have to know.”

“You’re-”

“Don’t tell me!” Dean shouts quickly, interrupting him. 

“You just said-”

“I know! Fuck! This is a mess! Just pretend I only said that  _ you _ are fucking good at this.”

“What is the phrase? It takes two to tango… We are  _ both  _ good at this.”

“No, it takes two to tango, it doesn’t take two to be good at the tango. Just one person needs to know how to tango and then two can tango!”

“Dean,” Cas rolls his eyes, “Do  _ you _ understand what you are saying?”

“No,” Dean sighs, “Not anymore.” 

“Me neither,” Cas giggles. 

“I liked sex without the condom!” Dean shouts randomly. 

Cas raises his eyebrows, “That’s good… Why?”

“I don’t know. We’re just like… Super close and also,” Dean licks his lips. “Don’t take this the wrong way but your ass is much softer than I thought it was going to be.”

_ “Softer?” _

“Don’t listen to me, I don’t know what I’m saying.”

“I have a soft ass,” Cas smiles like he’s proud of it.

Dean sighs and decides to play along. He was the one who started it anyway. “The softest,” Dean smiles. “So uh… How did that feel on your end? Weird?”

“Would you like to see for yourself?” Cas asks casually. 

Dean freezes. “See-” He swallows.

Cas tilts his head, “Yes.”

“For myself…” Dean processes. 

“If you would like,” Cas shrugs. “We could switch roles and then  _ you _ could feel for yourself!”

“S-” Dean bites his lip, “Switch.”

“Yes, switch.”

“Switch.”

Cas looks at him plainly for a second. “Are you well? Did I ‘break you’ again?” He asks. Dean doesn’t say anything, he just nods. “Okay,” Cas climbs off of Dean, “I am going to go get something to clean you up with,” Cas starts, “You can stay here and just… Think about it, alright?” Dean nods again. “There is absolutely  _ no pressure _ to decide any one thing specifically, and whatever you come up with, you can still change your mind, okay? No need to worry about anything.” Dean nods. “Okay,” Cas says finally. He presses a kiss against Dean’s cheek and walks out the door. Then point-two seconds later he walks back in. “I am naked,” He nods, “Fully naked.” He looks around for his underwear and his shirt to put back on before he leaves again. 

Dean is so out of it, he didn’t notice Cas left without clothes, and he couldn’t appreciate the humor of it all when Cas came back in. 

_ Switch. _

“Fuck!” Dean flinches. 

“Is this too hot?” Cas asks, pulling the rag away, panicked.

“No,” Dean shakes his head, “Sorry, you just scared me…” 

“I scared you?”

“Yeah,” Dean chuckles, “I didn’t hear you come in! You’re like a damn cat!”

“I’m not a cat,” Cas rolls his eyes with a smile as he starts wiping come off of Dean’s chest again. 

“This actually feels good,” Dean closes his eyes. 

“I’m glad,” Cas hums.

“You weren’t gone for very long,” Dean notes. 

“I was gone for about four minutes.”

“No,” Dean shakes his head, “You were gone for like twenty seconds.”

“I was gone  _ much _ longer than that.”

“Really?” Dean asks, confused. 

“Yes,” Cas nods. Dean is so out of it, it’s not even funny. 

“Did you- Uhm, did you, uh, clean yourself up?”

“Yes,” Cas nods. 

“Okay,” Dean bites his lip. “Sorry, I feel like I shoulda done that for you.”

“Don’t worry about it, Dean,” Cas smiles, setting the rag aside, then laying back down with him. 

“Hey, so,” Dean starts. “If I said I- If I uh- If I  _ didn’t _ want to… Ya know,” Dean shrugs, “Switch? Would you be mad?”

“No, of course not,” Cas says. “I wouldn’t be mad! If you said you never wanted to fornicate again, I still wouldn’t be mad.” 

“Woah,” Dean chuckles, “Let’s not go  _ there.” _

“I just mean that I will not be mad.” 

“Okay, well,” Dean grumbles. “I think,” Dean sighs. “Sorry, hold on.”

“Take your time,” Cas smiles and moves to lay on top of Dean. 

“Mgh,” Dean grunts low to himself. “I think we should- Mgh!” Dean grunts again. 

“We should…” Cas prompts. 

“I think we should switch,” Dean mumbles and rolls his eyes.

“Okay,” Cas smiles, “Let me know when you are ready and would like to try it!” 

“I’m ready,” Dean grumbles. “Maybe we can… Try tomorrow?” 

“If you would like,” Cas nods. 

“Okay,” Dean huffs.

“I think you are really going to enjoy it. If you find yourself feeling nervous at any point, I hope you understand that you can talk to me.”

“Ah,” Dean grumbles, “Cas, stop, I’m embarrassed!” Dean blushes. 

“I’m sorry,” Cas frowns. 

“No,” Dean grumbles.  _ “I’m  _ sorry. You’re being really nice,  _ I’m _ the idiot.”

“You’re not the idiot.”

“Cas,” Dean chuckles, “I’m as dumb as they come.”

“That’s not true.”

“Let me be dramatic,” Dean chuckles. “It helps me.”

“Okay,” Cas laughs with Dean. “And by the way,” Cas adds, “I think you’re  _ above _ average.”

“Yeah,” Dean chuckles. “I don’t believe you.”

“You should.”

“Nah,” Dean shakes his head, “You’re just saying that ‘cause you wanna have sex with me,” Dean chuckles. 

“Right,” Cas says sarcastically.  _ “That _ is why I’m saying this.”

Dean isn’t  _ thrilled _ about the idea of getting fucked in the ass, especially considering how  _ huge _ Cas’s dick is, but he can’t help but to be a little curious about it. As a hunter, he’s gotta be at least  _ a little _ curious. Or else he wouldn’t ever get anything done. And who knows. Everything so far has been nice, maybe bottoming for Cas will be just as nice. Even if he  _ is _ huge. 

Dean still hasn’t… Really tried anything. He kinda wanted to try it out first, then try sex with Cas, but he’s still too nervous. He wanted to  _ at least _ finger himself, then after that, he wanted to use that dildo he’s got hiding in his drawer. Except now it’s  _ two  _ dildos. And a vibrator. And a cock ring. Whoops! He may have gotten a little carried away.

He knows why he got the first dildo. He wanted to try it. Then he got the second one because, well, Cas is pretty big and he wanted a dildo that sorta matched his size. Then he got the cock ring because it’s supposed to make him last a little longer and he  _ always _ comes before Cas so he thought that would be nice. And honestly, he really can’t explain why he got the vibrator. What can he say, he was drawn to it. 

And  _ fuck! _ Not that this makes it worse, but he  _ definitely _ bought a plug online that’s supposed to come tomorrow, and he can’t stop thinking about it. And he doesn’t think it’s gonna fit in the drawer, so he’s gonna need to start taking the stuff out of their respective boxes. So he’s gonna have to deal with  _ those.  _ Who knows, maybe he’ll take ‘em somewhere and  _ burn them. _ A little, embarrassing, cardboard fire. He doesn’t know why he keeps buying things if he’s not gonna use them, but he can’t help it. He may have a problem. 

Damnit. Dean just wants to see what it’s like before he embarrasses himself with Cas. But he can’t. One time he was alone and thought he might try it. Then once he sat down he got too nervous and just ended up masturbating. Then a second time, he was alone, and this time, he finally took the first dildo out of the drawer which is a big step- considering it’s been in the drawer and nowhere else since he’s gotten it. He even took it out of its box! But once again, he got too nervous and he put all that away. Then he didn’t even masturbate. 

And now he and Cas are planning on trying tomorrow and Dean still has never put anything into his ass. He’s freaking out. Dean knows  _ he  _ was the one that told Cas tomorrow, so it’s his own fault. But he knows himself so he knows if he doesn’t set some sort of deadline then he’ll never do it. Now he said it out loud and it’s  _ happening. _

The next day, Cas doesn’t bring it up. So Dean  _ definitely _ doesn’t bring it up. The day goes on like normal except for one little thing. That little thing being that Dean can’t stop thinking about it. 

He’s getting fucked tonight. Cas is gonna fuck him in the ass. Oh god, there’s no coming back from that. Cas is  _ really _ gonna do him.  _ Really. _ This is real. Soon he’s gonna know what it feels like to have a dick in his ass. It’s really,  _ finally _ happening. 

“Cas,” Dean whispers to him nervously. Sam and Cas are sitting down in the map room reading. 

“Yes, Dean?”

“Uhm, so…” Dean whispers softer because if Sam heard what he was saying Dean would just  _ die. _ He’s just a short table length away. “Can I drink?”

“Alcohol?” Cas asks. 

“Yeah,” Dean nods. 

“Yes? Why wouldn’t you be allowed to?”

“Uhm,” Dean shrugs, “If I get a little bit,” Dean sighs, trying to get through this sentence. “If I’m like,  _ a little bit _ drunk, are you still gonna, you know…” Cas just stares at him, waiting for him to finish his sentence. Dean doesn’t wanna say it out loud so he just mouths the words,  _ “Fuck me?” _

“Oh,” Cas looks down to think for a moment. “I would prefer if you weren’t.”

“Okay,” Dean nods, “But just like…  _ A little bit. _ Not like  _ drunk,  _ but maybe a little bit  _ tipsy.” _

“As long as you are still able-minded enough to make decisions for yourself, I suppose that would be fine.”

“Awesome,” Dean sighs.

“Wait, Dean,” Cas pulls him back. “Is everything okay?” Cas whispers. 

“Yeah,” Dean nods, “Totally fine!”

“Are you sure?”

“No, Cas,” Dean shakes his head, “I’m nervous as hell! What do you want me to say?!” Dean says quickly but still whispering. Well, slightly above a whisper. 

“We don’t  _ have _ to do this right now,” Cas suggests, “We don’t have to do this  _ at all _ if you don't wish to.”

“Yeah but,” Dean swallows. “I’m  _ never _ gonna calm down. I’ll always be nervous. We just gotta do it and get it over with.”

“Get it over with?” Cas asks sadly.

“That’s not what I mean…” Dean glances at Sam. “Let’s talk about this later. Everything is fine, okay?”

“Alright,” Cas nods. 

“I’m gonna get a drink,” Dean smiles and kisses Cas quickly on the cheek before leaving. Dean thinks maybe a drink will help calm him down a little bit. Maybe two. Just beer. Just beer is fine. Cas probably won’t even notice. Maybe three. Three is okay. No, not three, three is too much, he doesn’t wanna freak Cas out, or make him feel bad, or keep him from doing what he wants to do. 

After Dean drinks his two beers, he walks back into the map room. “Goodnight, Sammy,” Dean smiles, “Long day, you know?”

“Yeah,” Sam agrees and nods, “Night, man.” 

Dean kisses Cas’s cheek again then makes eye contact with him before he walks out of the room. “I am  _ also _ going to say goodnight,” Cas closes his book and stands up. “It  _ is _ pretty late.”

“Yeah,” Sam yawns, “Jack is the smart one for going to bed like an  _ hour _ ago,” Sam chuckles. “Maybe I’ll go to bed too,” Sam stands up. 

“Alright,” Cas nods. Then goes to Dean’s room to find him. “Sam just went to bed,” Cas informs Dean.

“Noice,” Dean nods. He’s sitting on the bed. “I didn’t drink too much,” Dean says quickly, “I only had two beers. I didn’t even have a third…”

“Okay,” Cas nods, giggling. He sits on the bed with Dean. 

“So, I’m all good, right? You still wanna  _ fuck _ me, Cas?”

Cas smiles softly at him. “How nervous are you?” 

“I’m good!” Dean says, “I still wanna do this.”

“Okay,” Cas nods, “But you can be nervous and still want to do this.” 

“Well,” Dean shrugs, “I’m sorta freaking out, then. You’re gonna put stuff into my asshole and I’ve  _ never _ done that. Ever.” 

“That’s true,” Cas nods, just listening. 

“So I drank a little bit,” Dean chuckles, “And I think it’s helping.”

“Okay,” Cas nods. He wishes Dean  _ wasn’t  _ so freaked out and that he  _ didn’t _ have to drink in order to feel okay, but he understands. “New experiences can be frightening,” Cas sighs. 

“Cas,” Dean sighs and flops backward on the bed, “Don’t bullshit me, okay? Is this gonna feel good?”

“It’s going to feel  _ so _ good.”

“Really? It’s not just gonna be like,” Dean shrugs, “It’s not gonna be just a  _ feeling?” _

“What do you mean?” Cas asks. 

Dean sighs. “You promise it’s gonna feel good?” Dean asks again. 

“Yes.”

“Is it gonna hurt?”

“Perhaps at first,” Cas shrugs, “Because you aren’t used to it.”

“How bad is it gonna hurt?” Dean grimaces. 

“Not bad,” Cas says softly. 

“Mh,” Dean whines. “I can’t believe I’m gonna take it up the ass.”

Cas smiles fondly at him, “You don’t  _ have  _ to.” 

“No, I’m gonna…” Dean rolls his eyes. “Let’s just… Get this show on the road. How do we start?” Cas chuckles. “Oh gosh, now this seems forced, right?” Dean laughs nervously. “Here,” Dean sits up, “Tell you what,” Dean climbs into Cas’s lap, “We’ll make out a little bit until it feels normal, yeah?”

“Okay,” Cas nods with a smile, tackling Dean down onto the bed.

“Woah,” Dean chuckles. 

The kissing helps distract Dean a little bit. And also helps him relax. Maybe this isn’t such a big deal. Maybe it’s fine. Dean is probably just overreacting. Cas moves a hand down and starts to undo Dean’s belt. Then suddenly everything feels real again. Dean was right to be nervous about this. Oh god, it’s happening. His heart starts beating really fast. The kisses continue but Dean is distracted and not doing them very well. He knows he’s kissing Cas badly. Cas moves the kisses to Dean’s neck. Dean thinks it’s probably due to the fact that his kisses  _ sucked. _

Cas sits up on his knees down by Dean’s legs. “Are you still feeling like you want to try this?” Cas asks. 

Okay. Now is his chance to back down. He can say no. It’s fine. Cas said he won’t be mad. Dean never has to get fucked. He’s fine. He just has to say no. “Yes,” Dean squeaks. 

“Okay,” Cas nods, rubbing his hand firmly against Dean’s lower stomach. “You keep the lube in  _ this _ drawer, correct?” Cas asks, reaching for the drawer. 

Dean jerks up.  _ “No!” _ Cas tilts his head at him and retracts his arm. “Uh,” Dean chuckles. “I’ll get it… You- You take off your coat.”

“Okay,” Cas nods.

“Okay.” Dean positions himself awkwardly between Cas and the drawer so Cas can’t see into it while he gets the lube. Maybe he should keep the lube in a different drawer. Ugh, but then he’d have  _ two _ ‘night-time’ drawers, and who wants that? When Dean turns around with it, Cas holds his hand out. “Oh,” Dean swallows, passing the lube to Cas. 

“Alright,” Cas smiles, setting the lube down on the bed for a moment. “Dean,” Cas smiles, taking Dean’s shirt off of him, “You are so pretty…” 

“Cas,” Dean grumbles. “I’m not a girl.”

“What do you mean?” Cas asks, confused. Obviously Cas knows that, why does Dean mention it?

“I’m a boy,” Dean grunts. 

“Oh, my mistake,” Cas smiles, pushing Dean’s chest down so he is laying on his back again. “You are pretty  _ and _ manly.”

“Cas,” Dean rolls his eyes, hiding a chuckle. 

_ “Very _ pretty,” Cas continues. “Even when you’re nervous…” Cas starts pulling Dean’s pants down finally, but Dean feels his underwear coming with them so he grabs Cas’s wrist to stop him. “Are you alright?”

Dean swallows and waits for a second. They both just silently stare at each other. Dean blushes, “Yeah,” He lets go of Cas’s wrist. 

“Okay,” Cas smiles and takes Dean’s pants and underwear off. 

Dean covers his face with his hands. “Okay,” Dean swallows, “What do I have to do?”

“Well,” Cas shrugs, “I’d like to see your face,” He suggests. A few moments later, Dean sighs and drops his arms down and across his stomach. He won’t look at Cas. “It’s going to be okay, Dean, you really have nothing to be worried about-” Cas tries to open Dean’s legs but Dean won’t budge. “Dean,” Cas says softly, “I need you to spread your legs apart…”

“Okay, but… Can you tell me when you’re gonna put it in?” Dean asks nervously. “I don’t wanna be surprised.”

“Okay,” Cas nods with a chuckle. 

“Okay,” Dean swallows and opens his legs. “Oh  _ fuck,” _ He groans, closing his eyes. Cas hasn’t even done anything yet, he just feels really vulnerable. Cas is  _ really _ about to do it. Dean’s ass is getting  _ penetrated. _ First time ever. It’s gonna happen. It’s happening. 

“Oh, Dean!” Cas says like he’s got an idea, “If you would like me to, in order to relax this area a bit more,” Cas points to Dean’s ass, “I could perform oral on your-”

“No!” Dean says quickly. “I mean,” Dean calms down, “No,” He says a bit less harshly. “Never ever do that, okay?” Dean can’t believe Cas just suggested that. No way. Dean doesn’t want Cas’s tongue any closer to his asshole than it needs to be. 

“You may like it,” Cas argues. 

“Never. Ever.”

“Alright,” Cas rolls his eyes, “Never ever.”

“Thank you,” Dean sighs. 

“Are you ready?” Cas asks, uncapping the lube to put on his fingers.

“I’ll never be ready Cas, but yes, do it.”

“Okay,” Cas nods. 

“Mmh,” Dean whines unhappily. “Okay,” he nods. “This doesn’t feel bad.”

He just put one finger in. “Good,” Cas nods then starts adding pressure all around the rim of Dean’s ass. 

“Mh, okay,” Dean squeezes his eyes closed. “This is weird.”

“Does it feel okay?” Cas asks.

“It doesn’t hurt if that’s what you're asking.” Dean swallows. The thought is the weirdest part. Cas has a finger in his ass.  _ His ass. _ “Damn it,” Dean grumbles. 

Cas figures he should do something else so Dean doesn’t have the time or capacity to really  _ think _ about what’s going on. He’s an overthinker so a distraction would do him some good. Cas slides a second finger into Dean. 

“Woah,” Dean squeaks. “Okay,” Dean mumbles, “This is fine, this is fine,” He repeats to himself. 

“It doesn’t  _ really _ start to feel good until there is a second finger,” Cas informs him. 

“Hm,” Dean swallows. “It’s  _ big.” _

Well, technically, no it’s not, it’s just the most Dean’s ever had shoved into his ass. And maybe now that he’s thinking about it, Cas isn’t really doing a lot of shoving. 

“Dean,” Cas says softly, “This will feel better if you are relaxed.”

“I’m as relaxed as I can go,” Dean says. 

“Your  _ body _ is relaxed, yes,” Cas acknowledges, “But you need to  _ feel _ relaxed and this will be better.”

“How?” Dean squeaks. 

“It would obviously help if you were aroused, but it seems as though that has gone away. Take a deep breath, then I’m going to start moving my fingers a bit more. It’s going to feel so wonderful, I think you are going to like it.”

“Deep breath,” Dean sighs, “Okay, I can do that.”

“Okay,” Cas nods, “Try it now.”

Dean takes a deep breath and, as promised, Cas starts moving his fingers. “That’s actually,” Dean nods, “That’s kinda good…”

“Good,” Cas nods as he continues. 

“Awe,” Dean groans, “It feels like… Like stretching.”

“It  _ is _ stretching,” Cas suddenly reaches up to hold Dean’s dick which startles him a bit. Then Cas starts stroking. Dean likes that a lot and he focuses on that mostly. Cas can feel Dean’s body relax when he does. Then Cas stops because Dean is now fully hard. 

“Mh,” Dean moans softly. “This is actually pretty…” Dean grunts, “Okay, yeah,” Dean bites his lip. His back arches off the bed slightly. “I can see why people like-” Dean breaks to moan slightly, “Like this- Wow.”

“This feels good?” Cas asks, massaging his fingers deeper into Dean. 

“If I don’t think too much about it,” Dean swallows,  _ “Fuck,” _ Dean squeaks, “Yeah.” 

“See? What did I say-”

“Holy fuck!” Dean shouts, opening his eyes. His body sort of jerks and he’s panting really hard now. “What the hell was,” Dean breathes, “Was that?”

Cas tilts his head because he  _ thinks _ he knows. “This?” Cas asks, pushing his fingers against the spot again. 

Dean moans really loud. And then is confused as to why that happened. “Yes!” Dean swallows, “Fuck, yes, that.”

“That is your prostate,” Cas smiles and jams his fingers against it again. 

“Ohh…” Dean sings, “Yeah,” He swallows, “Do it again…”

Cas smiles as he does it again, glad Dean is legitimately enjoying this. “I can reach it if you are relaxed enough for it to be stimulated.”

“It feels good  _ everywhere,” _ Dean pants. Cas looks at Dean, his arms tight over his stomach and his fists balled. Like he doesn’t  _ quite _ know what to do with himself. His eyes are closed again and he’s biting his lip. Cas looks down and reaches for his dick again to jack him off. Dean moans immediately. Cas doesn’t do it for very long until he feels Dean push his hand away, “No, don't,” He pants, putting his hand over his dick protectively. 

“Why not?” Cas asks. 

“Because if I come right now, then you can’t fuck me!”

“I’m not  _ going _ to fuck you,” Cas says almost professionally. 

“You’re not?!” Dean asks, shocked. “Why not?”

“Because your body is new to this and I feel it’s best to take it slow.” That’s partly true. Cas isn’t going to tell him the  _ real reason,  _ which is that he wants Dean to get used to  _ feeling good _ because of this sort of stimulation. 

“What?” Dean mumbles. It’s hard to talk when Cas is still working his fingers inside of him. “We didn’t go slow with you…” Dean explains. 

“Yes,” Cas smiles softly, “But you are fragile.”

Dean squints, “And you’re not?”

“No,” Cas shakes his head. “Not as fragile as you.”

“But I thought you were gonna fuck me today.”

“I think we can just stick to the manual stimulation for today.” 

“Alright,” Dean huffs. He knows arguing with Cas won’t get him anywhere. He holds onto his dick rather firmly then starts jacking himself off.

“Do you want me to add another finger?” Cas asks. “Because if you do, I can do that now.”

“Oh,” Dean moans, “O- Okay,” He nods. 

“Alright,” Cas smiles, adding a third finger. 

Dean groans the moment Cas’s finger stretches him even more. “Fuck!” Dean groans. “Cas, can you,” He pants, “Can you do the thing again?”

“The thing?” Cas asks. He thinks Dean has to be talking about stimulation to his prostate. What else would ‘the thing’ be? “Alright,” Cas agrees. He just has to find it again. Cas lost a bit of his precision with the addition of a third finger, but he can still get to it if he figures out where it is. 

It takes Cas a moment to touch it again, but he gets it. “Ahh…” Dean groans. “Cas!”

“Are you going to come soon, Dean?” Dean nods. “Amazing,” Cas says softly, admiring Dean as he jerks himself off. At least for a little bit. He likes watching, but he is quickly overcome with a want to do it himself. He grabs Dean’s wrists so Dean stops. He opens his eyes to see why Cas stopped him. Cas doesn’t say anything, he just adjusts his position so he can suck Dean’s cock. 

“Oh  _ fuck,” _ Dean moans. “Fuck Cas,  _ fuck!”  _ He puts a hand into Cas’s hair, not really knowing what else to do. Everything just feels  _ really  _ good. Much better than he ever expected. And it doesn’t even hurt. “ _ Fuck-  _ Feels good,” Dean whines, “Good…” He says again. “Oh, Cas,” He whines loudly. “Gonna come, gonna come, gonna come!” He says quickly. Cas doesn't let up and soon Dean comes, moaning  _ very _ loud. Probably  _ too _ loud. Cas swallows and comes off of his dick, his fingers still buried deep. “Ah,” Dean whines, pushings Cas’s hand away to get his finger out of his ass, “Okay,” Dean squeaks, “Take ‘em out, take ‘em out!”

Cas slides his fingers gently out, “Did I hurt you?” He asks, worried. 

“No,” Dean pants, “No.”

“What happened?” Cas asks. 

“Hold on,” Dean pants, trying to catch his breath. Cas wants to talk but Dean just wants to breathe. “Holy fucking hell,” Dean sighs. “Okay,” Dean closes his eyes, “What was your question?”

“What happened?” Cas asks. 

“Oh,” Dean swallows, “I just got sensitive.”

“But you’re okay?”

“Yeah,” Dean nods. “Yeah, that felt really fucking good.”

“You liked it?” Cas asks, happily. 

“Fuck yeah,” Dean chuckles, opening his eyes and gazing at Cas. “I can’t believe that felt so good.”

“I’m glad that you enjoyed yourself,” Cas says with a smile. 

“Can we do it again?” Dean asks, biting his lip.

“Right now?”

“Yeah,” Dean swallows. He wants so badly to feel that thing again. It sent fire across his whole body and he wants it again. 

“Okay,” Cas nods. “If you can become erect again, I’ll stimulate you again,” Cas chuckles. 

“Ugh,” Dean rolls his eyes. “Fine.” He knows he can’t. At least not right this minute. “I still don’t know why you didn’t fuck me, but,” Dean shrugs and leaves it at that. 

“I want to finger you a few more times before we do that,” Cas explains. 

“What?” Dean asks. “A few more times?! Why?”

“So your body can be more ready!” Cas says, laying down next to Dean. Really so  _ Dean  _ can be ready. “It wouldn’t be wise to go from nothing to a penis. That is asking for too much.”

“Cas!” Dean whines, “We gotta do it  _ soon. _ Or else I’m gonna freak out. We just gotta do it! And get it out of the way!”

“I’m sorry, Dean, but I’m not going to enter you until I know you are ready.”

“Fuck,” Dean rolls his eyes. “Well, how long do you think that’s gonna take?” Dean asks. 

“I can guess?” Cas shrugs. 

“Damn it.”

“Be patient,” Cas sighs, wrapping his arms around Dean and laying his head on his chest, “It’s better this way.”

“Okay,” Dean rolls his eyes, still not 100% buying into it. “Hey, how come you never got naked? That’s not fair.”

“Oh,” Cas looks down, “My apologies. It didn’t seem important.” 

“It’s  _ very _ important,” Dean chuckles. “You’re my biggest turn-on.”

“Thank you,” Cas giggles. 

“Seriously though, if we do this again, and  _ you _ don’t take your clothes off, I’m gonna-”

“You’re ‘gonna’ what, Dean?” Cas asks, sternly. Dean gulps and says nothing. “What are you ‘gonna’ do?”

“Nothing,” Dean shakes his head, retreating.

“That’s what I suspected,” Cas smirks, nuzzling into Dean’s chest even more. How can Cas go from scary to fluff ball like that? “I think I should finger you again, later tonight. Would you be interested in that?” Cas asks. “It’s okay if you are too tired, I understand.”

“No,” Dean shakes his head, “I’m not! Finger me again,  _ please. _ Don’t let me fall asleep.”

“Alright,” Cas chuckles. “Then maybe… If you would like to, we can do it again in the morning?”

“Yeah, sure,” Dean nods, “Whatever we need to do to get me ready. I just wanna get fucked and get it done.”

“Once again, your attitude for this confuses me.”

**Notes for the Chapter:**

> Hehe, comment if you want to!!!


	2. Chapter 2

**Notes for the Chapter:**

> Haha, I love writing Dean when he’s nervous and stuff :)

Dean honestly really likes getting fingered by Cas. It wasn’t as scary as he thought it was going to be at all. He’s pretty happy about that. And Cas does this thing with his fingers, Cas told him what it was but he can’t remember, but it felt so good. Like nothing he’s ever felt before.  _ So good. _

He tries to convince himself that Cas’s dick will be no big deal. It’s probably the same, right? He can get fucked. He can do it. No need to be worried or anything. 

Like Cas suggested, Dean got fingered again last night. To completion. Then again in the morning. Then two more times throughout the day. Dean has really calmed down about getting fingered, thanks to Cas, and he actually looks forward to it a lot now. 

Then that night, Dean is going to go take a shower before bed and he asks Cas to shower with him. Cas agrees, then suggests he should finger Dean again. Dean was actually hoping Cas would do that, that’s why he invited him. That and he just likes showering with Cas. Dean just didn’t want to ask for it, it felt awkward to ask to be fingered. 

Once they got in, it was practically the first thing they did. Dean brought the lube. Cas positioned Dean to face the wall of the shower and spread his legs. He had to bend over a little bit, but not a lot. It was actually all very relaxing, especially with the warm water hitting him. He was oddly becoming more okay with the whole ‘butt thing’ the more Cas did this for him. It shocked him. This time, Cas suggested that Dean should refrain from jacking off because Cas thought he could get Dean to come just by doing this. And he was right. Which was weird. 

Then after, Dean took a shower like normal. He had to remind Cas, once again, to  _ do _ something. Dean really didn’t care what as long as it wasn’t just  _ staring. _ The first time Dean asked Cas to shower with him was  _ weird. _ It’s almost funny now, thinking back. Dean thought having his angel with him in the shower meant steamy, sexy fun times. Handjobs and making out and grinding, things like that. And it  _ kinda _ was. They made out. Cas touched Dean’s dick a little bit. Cas was just too concerned with Dean actually  _ showering _ to do anything real. He didn’t understand, he thought the purpose of a shower was solely to get clean so he kept encouraging Dean to comply. Then when Dean finally gave up trying to sex up Cas and gave into cleaning himself, Cas just stared at him. And it made Dean  _ really _ uncomfortable.

But after  _ this  _ shower, the two ended up in Dean’s room. Cas thought Dean would just go to bed so he tried cuddling with him. It worked for all of five seconds. “Can you uh… Can you do the thing again?” Dean asks. 

“Um,” Cas thinks, “Okay,” He nods. Dean gets up and awkwardly takes his pants off. Cas finds it a bit odd how Dean goes about this. Sort of like it’s a chore. Until it’s actually happening. Then Dean genuinely likes it. Cas also finds it odd that Dean wants to do this again right now. “Are you not tired?” 

“Meh,” Dean shrugs, getting lube and passing it to Cas. “I could fuck,” He says casually. 

“Is that why you would like me to manually stimulate you?”

“Yup,” Dean lays down and pulls back his legs. “Trying to get ready for your dick or whatever,” Dean says with fake confidence.

Cas rolls his eyes and gets into a position to finger Dean. “But you do like this, correct?” 

“Yeah,” Dean chuckles.

“Alright, good,” Cas pushes two lubed fingers into Dean. 

“But it  _ does _ have a purpose. I promise I’m not some sex maniac who needs to get off fifty times a day.”

“I know, Dean,” Cas nods seriously. Dean feels a bit awkward that Cas didn’t laugh no matter  _ how _ bad his excuse for a joke was. “You do know that you can finger yourself though, right?”

“Uh,” Dean groans, “Yeah, I know…”

Cas adds a third finger. He can do it quicker now since Dean is still pretty loose. 

Dean sighs heavily, eyes closed, just relaxing as Cas fingers him. Cas does it this time and it feels less intense. Which isn’t bad. It’s actually  _ really  _ soothing. He doesn’t feel close to coming yet, but that’s fine. He doesn’t need to. He just feels relaxed. And  _ really _ good. 

“What are you thinking about?” Cas asks. 

“Mmm,” Dean hums, “Just you…”

“Me?” Cas smiles, “You think about me?”

“Yeah,” Dean chuckles softly, “I think about ya all the time!”

“That’s nice,” Cas bites his lip. “What specifically right now?”

“You and how magical your fingers feel.”

“So you feel good then,” Cas comments. 

“Yeah…” Dean hums. 

“And relaxed?”

“Yeh…” 

“And happy?”

“Ye…”

“I can enter you this time if you would like,” Cas says bluntly. 

“What?”

“Only if you would like. There is no pressure to say yes.”

“Well, uh,” Dean gulps, “That’s why we're doing this, right?” Dean nervously chuckles. 

“I… Suppose…” Cas says like he doesn’t really suppose. 

“Well, uh,” Dean shrugs. “Put it in, I guess.”

Cas takes his fingers out. “Alright,” He nods. He can’t figure out why it feels weird so he’s hesitant. “You’re sure?” Cas asks, lining up with Dean. 

Dean picks his head but to look down and he sees Cas’s  _ huge cock _ extremely close to his ass hole and it’s- It’s frightening. “Cas,” Dean grunts, “Put it in.”

“Can you,” Cas thinks, “Can you please tell me you would like this to happen?” Cas wants to hear it because again, it feels weird. 

“I want this to happen,” Dean says but he doesn’t sound too sure of himself. “Put it in.”

“Dean-”

“Put it in. Put it in. Put it in. Put it in. Put it in,” Dean interrupts. 

“Okay,” Cas looks down and Dean watches slowly as he starts to move in. 

“Cas wait!” Dean shouts before Cas’s dick gets a chance to touch him,  _ “Don’t do it! I’m scared!!” _

“I knew it!” Cas says excitedly. He doesn’t mean to sound excited. He’s not excited because Dean is scared, he’s excited because he’s right! “Why didn’t you talk to me about it?!”

“I didn’t want you to know what a little  _ bitch _ I am! Too scared to get  _ fucked!” _

“Dean,” Cas scoffs, “That’s not what this is! You should have talked to me. I could have helped you.”

“You don’t understand! You’re so chill about sex stuff!”

“I won’t understand if you don’t  _ talk to me!” _ Cas argues. He puts his hands on Dean’s legs and pulls them back down so he is just laying on the bed. Cas sighs and sits down next to him. “Will you please talk to me about this?”

“No,” Dean shakes his head. He pulls the blanket over the lower half of his body to cover up. Cas is still unabashedly sitting with his dick out and no shame. Dean  _ wishes _ he could be that casual. “It’s too embarrassing, Cas, no.” Dean turns his face away from Cas. 

“Please?” Cas asks sweetly. 

Dean breathes out. It’s quiet for a few seconds before Dean talks again. “Okay,” He says softly.

“Okay,” Cas smiles, glad Dean is willing to talk. 

“What if… What if it doesn’t feel good?”

“Then we’ll stop.”

“What if it hurts too bad?” Dean sounds a bit more worried about this question.

“Then we will stop and I will make it feel better.”

“How?!” Dean panics. 

“I can soothe you with grace,” Cas offers gently. 

“Okay,” Dean nods, “Well, what if something rips!?”

“Nothing is going to rip.”

“What if you’re too big for me?!” 

“Your body will stretch-”

_ “What if your dick gets stuck?!” _

“It’s not going to-”

_ “WHAT IF EVERYTHING TURNS INSIDE OUT?!” _ Dean panics. 

“It’s not-”

_ “THAT CAN HAPPEN, CAS! I LOOKED IT UP!” _

“Okay,” Cas sighs, “Maybe we shouldn’t be doing this-”

“Oh my god. You think it’s gonna happen  _ too?!” _

“No!” Cas says quickly. “You’re being completely irrational. That’s not going to happen!”

“It’s not?” Dean asks. 

“No!”

“Are you sure?”

“Yes!” Cas huffs. 

“Then why shouldn’t we do it?” Dean asks. 

“Because you’re not ready like I thought you were,” Cas sighs. 

“What?”

“It’s okay, Dean, if you don’t want to do this. I understand that it can be nerve-racking. I had no idea the  _ extent _ it could be,” Cas chuckles, “We can try another time, or never if you would like.”

“Wait, Cas,” Dean sighs. “I want to…”

“It sounds like it may not be the best time,” Cas says softly, trying to hide his disappointment. 

“Wait,” Dean grumbles, putting a hand on Cas’s thigh. “I  _ want _ you to do this. I’m scared, but… But I can get over it.”

“How?” Cas asks. “Did talking help?”

Dean doesn’t want to say yes. “A little bit. You’re right. My ass isn’t gonna flip inside out. Even though it can, that’s a real thing.”

“Only if no caution is taken.”

“Yeah…” Dean nods. “And your dick probably  _ won’t _ get stuck.”

“It most certainly  _ will not _ get stuck,” Cas chuckles, taking Dean’s hand in his. 

“Well, there’s always a chance,” Dean shrugs. 

“No,” Cas shakes his head, “There really  _ isn’t.” _

“And you probably aren’t too big for me, but maybe you are.”

“If you find discomfort in this due to the size of my penis we will stop. And if you still want to fornicate, your hole can be trained and stretched to accommodate size better. It  _ is _ a muscle after all.”

“Okay,” Dean takes a deep breath. “Cas…” Dean swallows.

“Yes?”

“What if I fart?” Dean asks faintly. 

Cas can tell he is genuinely worried about this. “It won’t be a big deal, and it’s completely natural.”

“I’d be so embarrassed Cas, don’t make fun of me!”

“I would never,” Cas assures him. “But if that  _ were _ to happen, what would you like me to do?”

“Kill me.”

“Dean,” Cas shakes his head. “I was talking more along the lines of, would you like me to comfort you and tell you it’s okay or would you like me to ignore it?”

“Kill me.”

“Dean,” Cas squeezes Dean’s hand for a moment. “That isn’t funny.”

“Do you think that’s gonna happen?” Dean asks nervously. 

“Probably not,” Cas shakes his head. 

“Then I don’t wanna talk about it.”

“Alright.”

“Okay,” Dean sighs, “Can you be gentle?”

“Yes,” Cas nods. 

_ “Really _ gentle?” Dean asks. 

“Yes.”

“Promise?”

“Of course, Dean,” Cas smiles. 

“Okay,” Dean sighs again. “I’m fragile, you know…” Dean jokes because that’s what Cas said to  _ him. _

“Yes, I know,” Cas chuckles. 

“Okay,” Dean bites his lip. “Do it.”

“You would like me to-”

“Enter me,” Dean rolls his eyes, “Yeah, but… Could you not call it that?” Dean asks. 

“Okay,” Cas agrees, “Would you like me to  _ fuck you?” _

“Yeah,” Dean chuckles, “Yeah, that’s more like it.”

“Alright,” Cas smiles and gets to where he needs to be again. He pulls the blanket off of Dean and Dean raises his knees back up. “I’m going to add more lube,” Cas says finding and opening the bottle, “So don’t be surprised.” Cas’s fingers push into his ass again and Dean gets goosebumps at how cold the lube is. 

“Auh,” Dean groans. “I can’t believe this is happening right now,” Dean bites his lip. “It’s exciting but also terrifying.”

“What makes you want to try this if you are so terrified?”

“Because,” Dean chuckles. “I gotta know.”

Cas pulls his fingers out, “Know what?”

“I gotta know how it feels or I’ll always wonder.” 

“Okay,” Cas nods, holding onto Dean’s hips as he lines up. 

“Go slow!” Dean says. 

“I will,” Cas nods. 

“Be gentle!”

“Okay,” Cas says patiently. 

“Okay…” Dean is breathing hard again as he tries to calm down. He closes his eyes and tries to relax. “This is fine,” Dean mumbles to himself. “Easy, Cas…”

“Alright, Dean,” Cas chuckles and starts to slide in. 

“Mmh…” Dean grumbles as Cas gets deeper. “Fuck, you’re huge,” Dean swallows. “Oh fuck, dude.”

“I’m almost completely in,” Cas informs him. 

“You’re not even all the way in yet?!” Dean pants. Cas is going very slowly so Dean can adjust. “Ah- Okay,” Dean swallows, “That’s as far as it can go, babe. It can’t go in any farther.”

“Dean,” Cas says softly, “I won’t go farther if you would like, but I  _ can _ go farther .”

“No, it’s impossible.”

“It’s not,” Cas chuckles. 

“It feels impossible,” Dean squeaks. “Okay yeah, if you think you can… Go ahead. Let’s see.” Cas hums softly once he’s entirely in. “Fuck. There’s a literal dick in my ass right now,” Dean swallows. “Your dick is inside of me- It’s really- This is real. This is happening.”

“How do you feel?” Cas asks. 

“I don’t know,” Dean bites his lip. “This is weird. Your dick is in my ass!”

“I’m going to move now, alright?” Cas says. 

“Okay,” Dean squeaks. He closes his eyes again and focuses on relaxing. Cas starts sliding out and in very slowly. “Ohh… This is-” Dean swallows. “Mmg!” He groans. 

“Do you feel okay?” Cas asks.

“Mmhm,” Dean nods. “Yeah, really good.” Dean can feel himself shaking a little bit. But really, it feels kinda good. Filling? If that’s a feeling, then that’s what it feels like. Dean sort of likes it. Cas’s dick is so much bigger than his fingers, it’s unreal. It really doesn’t feel the same like Dean thought it would  _ at all. _ “Oh, Cas,” Dean bites his lip.

“Are you alright?” Cas asks, stopping briefly. 

“Yeah,” Dean nods, “So good… Keep going.” Cas smiles faintly and starts moving again. “Yeah,” Dean hums, delighted. Dean reaches for his dick and starts jerking off as Cas does his thing. Cas appreciates the fact that Dean feels comfortable and well enough to do it. “Hey, Cas?”

“Yes?” Cas asks. 

“Can you go faster?” Dean sounds a little unsure when he asks. 

“Yes-”

“Just a little bit!”

“Okay,” Cas nods and he goes a little bit faster. 

“Ugh,” Dean moans, “Yeah, that feels good!” Dean starts jacking off a bit faster as well. “Oh, Cas,” Dean whines, “We should do this more often,” Dean swallows. 

“I agree,” Cas smiles, happy that Dean is happy. 

“I mean it,” Dean pants, “How- How are you? You feel- You feel good?” 

“Very good,” Cas hums. Cas would like it better if he could thrust a little bit more, but he still is feeling good. 

“Mgh,” Dean sighs, “Harder, Cas…”

“Harder?” Cas asks for clarification. 

“Yeah,” Dean nods. Cas starts pushing into Dean a bit harder and Dean instantly groans. “Mmh!” Dean lets go of his dick. “So big, you’re so big.”

“You are so good at this, Dean,” Cas smiles. 

“I haven’t done anything, Cas,” Dean chuckles but that turns into a groan. “Oh  _ fuck, Cas. _ Faster. Please, faster!”

“Are you sure?” Cas asks. 

“Yeah,” Dean pants. “I need you to go faster.”

“Okay,” Cas bites his bottom lip and starts thrusting into Dean. 

“Fuck!” Dean pants. “Yeah, like that!”

“Good,” Cas smiles. It feels  _ much _ better now that Cas can speed up like he wants. “How does it feel?” 

“Feels good,” Dean nods. “Really-” Dean is interrupted by a moan. He closes his eyes tighter and just tries to feel Cas. Not think. Just feel. Soon he’s panting  _ very _ hard. “Fuck!” He keeps cursing. 

Cas continues ruthlessly driving his hips into Dean and Dean is falling apart. This feels way better than he could have imagined. It’s not scary. It’s awesome. It feels  _ awesome. _

“Fuck!” Dean pants again. Cas hits that spot that Dean likes. “Ahh, Cas!” Dean groans. His back arches off the bed, “Cas, again!” Cas tries to hit it again but it takes a few thrusts to get it right. “Gah!” But he finally does. “Aww, Cas,” Dean whines. “I’m close.” 

“Alright,” Cas grunts, thrusting into him again. Cas isn’t exactly close, but he does feel fantastic. He figured he would like it, he’s happy that he’s right. He’s even happier that  _ Dean _ likes this. The more Dean enjoys himself, the more Cas enjoys himself. 

“Cas,” Dean pants. “Cas, Cas, Cas…” Dean starts jacking off again, but only for a moment before he comes all over himself. “Fuck!” Dean whines and starts to squirm. 

Cas pulls out of Dean very slowly, watching him lay on the bed, catching his breath. “You are truly the most beautiful man ever created.”

“Cas,” Dean grumbles and blushes. He doesn’t like when Cas says things like that, it’s embarrassing and makes his face hot. But deep down he kinda does like it. It’s nice to be admired. Especially by someone as great as Cas. “Are you gonna come?” Dean pants. “Do you want help?”

Cas chuckles and shakes his head, “No.”

“No, you aren’t gonna come? Or no, you don’t want help? What’s wrong with my help?”

“Dean,” Cas chuckles again, “I love your help. It’s amazing help, honestly! But now, I want to just… Talk to you.”

“Oh,” Dean looks down, still trying to calm his breathing down. “Well, that’s not fair.”

“What?”

“You should come, Cas.”

“It’s not necessary,” Cas smiles and traces a finger through the come on Dean’s stomach. 

“It is to me!” Dean grumbles. Cas doesn’t reply. “What are you doing?” Dean finally asks. 

“Just looking at all this ejaculate. It’s quite a large amount this time.”

Dean doesn’t know if he should be embarrassed about that or not. He is, a little. “I guess,” he mumbles. Cas smiles at him. “There’s come in my belly button…” Dean points out. He doesn’t know why he said that, it just came out. It’s a weird feeling and it’s never happened to him before. He glances down and sees how filled it is. It makes him a little squirmy. 

“Yes,” Cas smiles lazily like he’s enjoying the sight of it. 

Then Cas leans down and laps the come out of Dean’s belly button. “Ah, Cas!” Dean says, slightly horrified. “Fuck.”

“What?” Cas raises his head and smiles at him, amused by Dean’s reaction. 

“Why do you do that?”

“Because,” Cas watches as Dean’s face reddens. “You enjoy it.” He looks away from Cas, slightly embarrassed. He would pull the blanket back up to cover himself, but he’s still dirty and he doesn’t want to ruin the blanket. “How are you feeling?” Cas asks.

Dean closes his eyes and just nods. Cas is slightly confused at this because he didn’t ask a yes or no question. A few silent moments go by as Cas waits for Dean to use words. “Good.”

Cas, now a little worried, nods. “That’s good…” He wishes Dean would elaborate a little bit. He wants to talk about everything. Towards the middle and  _ definitely  _ the end, Dean was  _ very _ enthusiastic. Cas hesitates to talk more. He wants to make a joke because Dean appreciates humor in situations like these. But no joke comes to mind. “I’m going to go get you a warm rag-”

“Wait,” Dean grabs Cas’s wrist to stop him. “Not yet.”

Cas doesn’t ask why, he just nods simply, “Okay.” Cas has no idea when the mood shifted but he knows that it did. “Dean, did you- It seemed like you enjoyed that, did you?”

Dean nods, “Yeah,” he assures. “But,” Dean shrugs. Cas looks down, hiding that he’s upset. “I don’t know, don’t you think that was a little weird?”

Cas swallows, “I suppose.” He shrugs. 

“It was really awkward.”

“Why?”

“Well, you know… We talked a lot-”

“Communication is important-” 

“I know,” Dean nods. “But it kinda made it awkward. And weird. And embarrassing…”

“I’m sorry,” Cas won’t look at him. 

“Yeah, but I’m sure next time will be better because we already kinda know what to do!”

“What?”

“You know,” Dean chuckles, “We won’t have to awkwardly talk as much. Less pausing to ask if ‘that feels okay.’ You can just…  _ Fuck _ me.”

Cas’s face lights up. “You wish to do this again?” He sounds surprised. 

“Uh,” Dean chuckles, “Hell yeah. That was close to the best orgasm I’ve ever had in my life. I feel like it’s gonna just get better from here, right?” 

“Really?” Cas smiles, climbing over Dean. 

Dean is shocked by Cas’s sudden movements. “Yeah! I’d ask to do it again if I could.”

“You would like to fornicate again, right now?!”

Dean chuckles at how excited Cas is. “Yeah, that’s why I didn’t want you to wipe me off yet.”

“Oh, Dean!” Cas smiles. He leans down quickly and smashes their lips together. “Tell me more!”

“Like what?”

“Everything.”

Dean laughs nervously. “Uh,” Dean shrugs and looks away, “I think I uh, like it better when you are…” How does he put this? “Less… Gentle.”

“I think you like it more that way as well!” Cas adds. 

“Yeah,” Dean smiles, “We should do this more.”

“Yes?” 

“Yes!” Dean giggles with Cas. “And you can be maybe…” He leans up, closer to Cas’s lips again. Cas gets the message. “Maybe a little rougher?”

Cas kisses him softly for a few moments. “I’d like that-”

“Oh!” Dean shouts, “How- How’d that feel for  _ you?”  _

“It was very nice. Your  _ ass  _ is quite tight.”

“‘Very nice,’” Dean mimics in a crude impression of Cas, “‘Your ass is quite tight.’”

“Dean,” Cas chuckles. 

“‘Dean,’” Dean mimics again. “But you felt good though?”

“Yes. I’d like to be inside of you again.”

“And you’ll come this time?”

“Inside of you?” Cas lowers his voice. Dean swallows and gets goosebumps. “Without a condom?”

Dean wiggles. “Yeah… No- No condom…”

“None.”

“None.”

“You really seem to like that concept.”

“I’ve never been as close to someone as I am with you.” 

Cas smiles. He feels the same, but that goes without saying. “So the lack of a condom is a measurement of closeness to you?” Dean nods. “Alright, I can understand that.”

“Hey, Cas?” 

“Yes?”

“I’m cold.”

Cas moves a bit, “Would you like me to lift the blanket?”

“No,” Dean shakes his head, “I’m dirty. I don’t wanna get the bedding dirty too.”

“I could clean you.”

“No, because you’re gonna fuck me again.”

“Oh,” Cas chuckles. “Well I could…” Cas climbs in next to Dean, holding him to keep him warm. 

Perfect, just what Dean wanted. He asked around it. He knows Cas prefers he ask directly but he thinks he’s been awfully open about his feelings already. Definitely enough for one night. 

“Cas,” Dean sighs, snuggling into Cas, “You’re strong.”

“Are you asking or are you telling?” Cas giggles. 

“Well, I was thinking… You could fuck me against walls and stuff.”

“If you would like.”

“And you could…” Dean smiles but he trails off. Just thinking. Quiet for a while. “Oh, you can do all sorts of stuff to me.”

“I  _ want _ to do all sorts of stuff to you.”

“Mmh,” Dean hums. “Start now.”

“Now?” Cas chuckles. 

“Yeah, now!”

Cas reaches his hand down to fondle Dean. He wants to see if he really  _ can _ get it up again. Dean closes his eyes and really tries to focus. “Dean,” Cas chuckles. 

“Okay, fine. I’m not really ready yet.”

“No,” Cas chuckles, “Not really.” 

“But I just wanna feel you inside of me again! And again! And again!”

“Are you sure you would like to fornicate again  _ tonight?” _

“Yeah,” Dean nods, “Why?”

“Well,” Cas shrugs, “You have ejaculated many times today.” 

“So what are you saying, I’m capped?”

“No,” Cas chuckles. Well at least, probably not. “I am just surprised you are not tired.”

“I  _ am _ tired.” 

“We can do this another time. I’m not going anywhere.”

Dean smiles softly. “Yeah but, it feels so good. You don’t understand… Well actually, maybe you do. But I wanna do it again tonight! Is that still okay?” 

“Yes, of course,” Cas says calmly. 

“Mmh,” Dean hums. “I’ll let you know when I get hard.”

“I’m sure I will notice,” Cas starts kissing him again. 

**Notes for the Chapter:**

> Thank you for reading!!! Comment if you feel like it! They make me so happy!


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